PL215430B1 - Process for the preparation of 2'-hydroxydihydrochalcone - Google Patents
Process for the preparation of 2'-hydroxydihydrochalconeInfo
- Publication number
- PL215430B1 PL215430B1 PL399423A PL39942312A PL215430B1 PL 215430 B1 PL215430 B1 PL 215430B1 PL 399423 A PL399423 A PL 399423A PL 39942312 A PL39942312 A PL 39942312A PL 215430 B1 PL215430 B1 PL 215430B1
- Authority
- PL
- Poland
- Prior art keywords
- carried out
- hydroxydihydrochalcone
- preparation
- hours
- substrate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 8
- JCPGMXJLFWGRMZ-UHFFFAOYSA-N 2-hydroxy-beta-phenylpropiophenone Natural products OC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JCPGMXJLFWGRMZ-UHFFFAOYSA-N 0.000 title claims description 7
- BJGDMOPWBQPTDI-UHFFFAOYSA-N 3-cyclohexa-2,4-dien-1-yl-1-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC=CC=C1C(=O)C=CC1C=CC=CC1 BJGDMOPWBQPTDI-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 241000187562 Rhodococcus sp. Species 0.000 claims description 5
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 229930003949 flavanone Natural products 0.000 claims description 5
- 150000002207 flavanone derivatives Chemical class 0.000 claims description 5
- 235000011981 flavanones Nutrition 0.000 claims description 5
- 230000009466 transformation Effects 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 238000003385 ring cleavage reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 230000002906 microbiologic effect Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- AETKQQBRKSELEL-UHFFFAOYSA-N (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one Natural products OC1=CC=CC=C1C(=O)C=CC1=CC=CC=C1 AETKQQBRKSELEL-UHFFFAOYSA-N 0.000 description 3
- AETKQQBRKSELEL-ZHACJKMWSA-N 2'-hydroxychalcone Chemical compound OC1=CC=CC=C1C(=O)\C=C\C1=CC=CC=C1 AETKQQBRKSELEL-ZHACJKMWSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003005 anticarcinogenic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000011944 chemoselective reduction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000013615 non-nutritive sweetener Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania 2'-hydroksydihydrochalkonu, o wzorze 3 przedstawionym na rysunku.The subject of the invention is a process for the preparation of 2'-hydroxydihydrochalcone of formula III shown in the drawing.
Sposób, według wynalazku może znaleźć zastosowanie w przemyśle spożywczym do produkcji niskokalorycznych środków słodzących, pochodzenia naturalnego (Encyclopedia of Food Science, Food Technology and Nutrition. Academic Press, London 1993, Krutosikowa A., Uher M: Naturalne i syntetyczne substancje o słodkim smaku. PWN, Warszawa 1990) oraz w przemyśle farmaceutycznym do wytwarzania środków przeciwzapalnych, antykancerogennych i antyoksydacyjnych.The method according to the invention may find application in the food industry for the production of low-calorie sweeteners of natural origin (Encyclopedia of Food Science, Food Technology and Nutrition. Academic Press, London 1993, Krutosikowa A., Uher M: Natural and synthetic sweet-tasting substances. PWN, Warsaw 1990) and in the pharmaceutical industry for the production of anti-inflammatory, anti-carcinogenic and antioxidant agents.
Znane są sposoby chemicznego uwodornienia 2'-hydroksychalkonu katalizatorem palladowym osadzonym na węglu aktywnym. (J.K. Buolamwini, A. Gupte, Bioorganic & Medicinal Chemistry Letters, 2009, vol. 19, s. 917-921).There are known methods of chemical hydrogenation of 2'-hydroxychalcone with a palladium catalyst supported on activated carbon. (J.K. Buolamwini, A. Gupte, Bioorganic & Medicinal Chemistry Letters, 2009, vol. 19, pp. 917-921).
Znane są sposoby chemicznej syntezy 2'-hydroksydihydrochalkonu z udziałem wodoru przy ciśnieniu 2,5 bar (J.K. Buolamwini, A. Gupte, 2009, vol 19, s. 917-921).There are known methods of chemical synthesis of 2'-hydroxydihydrochalcone with the participation of hydrogen at a pressure of 2.5 bar (J.K. Buolamwini, A. Gupte, 2009, vol 19, pp. 917-921).
Opracowano także metodę chemoselektywnej redukcji α,β-nienasyconego wiązania olefinowego 2'-hydroksychalkonu z udziałem rodu jako katalizatora (Z. Baάn, Z. Finta, G. Keglevich, I. Hermecz,A method of chemoselective reduction of the α, β-unsaturated olefinic bond of 2'-hydroxychalkon with rhodium as a catalyst was also developed (Z. Baάn, Z. Finta, G. Keglevich, I. Hermecz,
Green Chemistry, 2009, vol. 11, s. 1937-1940).Green Chemistry, 2009, vol. 11, pp. 1937-1940).
Znany jest sposób chemicznej syntezy 2'-hydroksydihydrochalkonu a następnie regioselektywnej redukcji wiązania węgiel-węgiel otrzymanego ketonu katalizowanej solami rutenu w dioksanie w temperaturze 80°C (C.S. Cho, S.C. Shim, Journal of Organolmetalic Chemistry, 2006, vol. 691,There is a known method of chemical synthesis of 2'-hydroxydihydrochalcone followed by regioselective reduction of the carbon-carbon bond of the obtained ketone catalyzed by ruthenium salts in dioxane at 80 ° C (C.S. Cho, S.C. Shim, Journal of Organolmetalic Chemistry, 2006, vol. 691,
s. 4329-4332).pp. 4329-4332).
Znany jest sposób otrzymywania 2'-hydroksydihydrochalkonu na drodze mikrobiologicznego rozszczepienia pierścienia C flawanonu za pomocą Penicillium chrysogenum 10002 K (Abdel-Rahim S. Ibrahim, Yusuf J. Abul-Hajj; Journal of Natural Products, 1990, vol. 53, nr 3, s. 644).There is known a method for the preparation of 2'-hydroxydihydroochalcone by microbial cleavage of the C-ring of flavanone with Penicillium chrysogenum 10002 K (Abdel-Rahim S. Ibrahim, Yusuf J. Abul-Hajj; Journal of Natural Products, 1990, vol. 53, no. 3, p. 644).
W dostępnej literaturze nie znaleziono doniesień o sposobie otrzymywania 2'-hydroksydihydrochalkonu z udziałem szczepów bakterii z rodzaju Rhodococcus sp.In the available literature, no reports were found on the method of obtaining 2'-hydroxydihydrochalcone with the use of strains of the Rhodococcus sp.
Istota wynalazku polega na tym, że reakcję rozszczepienia pierścienia C prowadzi się za pomocą systemu enzymatycznego szczepu bakterii z rodzaju Rhodococcus sp. przy czym substrat dodaje się po upływie 24 - 96 godzin, a reakcję prowadzi się w temperaturze 283 - 317K. Mieszaninę transformacyjną ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą, ekstrakt osusza się siarczanem (VI) sodu, odparowuje rozpuszczalnik i tak powstały surowy produkt, oczyszcza chromatograficznie.The essence of the invention lies in the fact that the C-ring cleavage reaction is carried out with the enzyme system of a strain of bacteria of the genus Rhodococcus sp. With the substrate being added after 24 - 96 hours, and the reaction carried out at the temperature of 283 - 317K. The transformation mixture is extracted with a water-immiscible organic solvent, the extract is dried with sodium sulphate, the solvent is evaporated and the crude product thus obtained is purified by chromatography.
Korzystnie jest, gdy proces rozszczepienia prowadzi się wodną kulturą, przy ciągłym mieszaniu, w temperaturze 288 - 307K.Preferably, the cleavage process is carried out with an aqueous culture under constant stirring, at a temperature of 288-307K.
Korzystnie także jest, gdy substrat dodaje się po upływie 48 godzin.It is also preferred that the substrate is added after 48 hours.
Dodatkowo korzystnie jest, gdy rozpuszczalnikiem organicznym jest octan etylu.In addition, it is preferred that the organic solvent is ethyl acetate.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach bakterii Rhodococcus sp., następuje reakcja rozszczepienia pierścienia C flawanonu, a następnie hydrogenacja α,β-nienasyconego wiązania olefinowego substratu w wyniku czego otrzymuje się 2'-hydroksydihydrochalkon.In accordance with the invention, as a result of the action of the enzyme system contained in the cells of Rhodococcus sp. Bacteria, the C-ring cleavage reaction of the flavanone takes place, followed by hydrogenation of the α, β-unsaturated bond of the olefinic substrate, resulting in the preparation of 2'-hydroxydihydroochalcone.
Uzyskany w ten sposób produkt wydziela się z kultury mikroorganizmu, znanym sposobem przez ekstrakcję oraz oczyszcza za pomocą chromatografii.The product obtained in this way is separated from the culture of the microorganism by a known extraction method and purified by chromatography.
Zasadniczą zaletą wynalazku jest otrzymanie 2'-hydroksydihydrochalkonu z dostępnego komercyjnie taniego substratu, z całkowitą wydajnością izolowaną równą 44%, w temperaturze pokojowej, przy ciśnieniu atmosferycznym, w środowisku wodnym i w pH bliskim obojętnego.The main advantage of the invention is the preparation of 2'-hydroxydihydroochalcone from a commercially available cheap substrate, with a total isolated yield of 44%, at room temperature, atmospheric pressure, in an aqueous environment and at a pH close to neutral.
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d 1. Do kolby płaskodennej o pojemności 2000 cm3, w której znajduje się 250 cm3 sterylnej pożywki zawierającej 4 g glukozy, 10 g ekstraktu maltozowego, 4 g ekstraktu drożdżowego, g węglanu wapnia, wprowadza się szczep Rhodococcus sp. Po 48 godzinach wzrostu dodaje się 3 mg flawanonu, o wzorze 1, rozpuszczonego w 1 cm3 acetonu. Transformację prowadzi się przy ciągłym wstrząsaniu przez 7 dni w temperaturze pokojowej. Następnie uzyskaną mieszaninę transformacyjną ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem(VI) sodu i odparowuje rozpuszczalnik. Otrzymuje się 62 mg surowego produktu, który oczyszcza się chromatograficznie na żelu krzemionkowym, używając jako eluentu mieszaniny heksan - eter dietylowy - dichlorometan w stosunku objętościowym 8:0,5:1,5. Na tej drodze otrzymuje się 7,3 mg 2'-hydroksychalkonu z 30%-owąExample 1. To a flat-bottom flask with capacity of 2000 cm 3, which is 250 cm 3 of sterile medium consisting of 4 g of glucose, 10 g maltose extract, 4 g of yeast extract g of calcium carbonate is introduced into a strain of Rhodococcus sp. After For 48 hours of growth, 3 mg of flavanone, formula I, dissolved in 1 cm 3 of acetone, are added. The transformation is carried out under continuous shaking for 7 days at room temperature. The resulting transformation mixture was then extracted three times with ethyl acetate, dried with anhydrous sodium sulfate and the solvent was evaporated. 62 mg of crude product are obtained which are purified by chromatography on silica gel using a hexane-diethyl ether-dichloromethane mixture in a volume ratio of 8: 0.5: 1.5 as eluent. In this way, 7.3 mg of 2'-hydroxychalcone with 30% strength are obtained
PL 215 430 B1 wydajnością oraz 3,3 mg 2'-hydroksydihydrochalkonu z 44%-ową wydajnością (w stosunku do 2'-hydroksychalkonu).% Yield and 3.3 mg of 2'-hydroxydihydrochalcone in 44% yield (in relation to 2'-hydroxychalcone).
P r z y k ł a d 2: Postępuje się jak w przykładzie 1, z tym, że do zaszczepionej pożywki, dodaje się flawanon po 72 godzinach.Example 2 The procedure of Example 1 is followed, except that flavanone is added to the inoculated medium after 72 hours.
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (300 MHz, CDCI3) δ: 12,28 (1H, s), 7,73 (1H, dd, J = 8,0 Hz, J=1,5 Hz), 7,29 (2H, m), 7,25 (2H, m), 7,21 (1H, m), 7,19 (1H, m), 6,96 (1H, dd, J = 8,4, J=0,7), 6,86 (1H, td, J = 8,0 Hz, J = 0,9 Hz), 3,32 (2H, t, J =15,3 Hz, J = 7,3 Hz), 3,06 (2H, t, J = 15,3 Hz, J = 8,0 Hz). 1 H NMR (300 MHz, CDCl 3) δ: 12.28 (1H, s), 7.73 (1H, dd, J = 8.0 Hz, J = 1.5 Hz), 7.29 (2H, m ), 7.25 (2H, m), 7.21 (1H, m), 7.19 (1H, m), 6.96 (1H, dd, J = 8.4, J = 0.7), 6.86 (1H, td, J = 8.0Hz, J = 0.9Hz), 3.32 (2H, t, J = 15.3Hz, J = 7.3Hz), 3.06 ( 2H, t, J = 15.3 Hz, J = 8.0 Hz).
UV Xmax (nm): 324, 252, 215.UV Xmax (nm): 324, 252, 215.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL399423A PL215430B1 (en) | 2012-06-04 | 2012-06-04 | Process for the preparation of 2'-hydroxydihydrochalcone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL399423A PL215430B1 (en) | 2012-06-04 | 2012-06-04 | Process for the preparation of 2'-hydroxydihydrochalcone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL399423A1 PL399423A1 (en) | 2013-03-04 |
| PL215430B1 true PL215430B1 (en) | 2013-12-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| PL399423A PL215430B1 (en) | 2012-06-04 | 2012-06-04 | Process for the preparation of 2'-hydroxydihydrochalcone |
Country Status (1)
| Country | Link |
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| PL (1) | PL215430B1 (en) |
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2012
- 2012-06-04 PL PL399423A patent/PL215430B1/en unknown
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| Publication number | Publication date |
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| PL399423A1 (en) | 2013-03-04 |
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